Triethylamine → HCID 86629449, compound

HRID 599291Notes

Reaction equation

O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH2:9]([NH:11][C:12]1[C:17]([CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=2)=[CH:16][N:15]=[C:14]([N:30]([O:32][CH3:33])[CH3:31])[CH:13]=1)[CH3:10].CCN(CC)CC>>[CH2:9]([N:11]1[C:12]2[CH:13]=[C:14]([N:30]([O:32][CH3:33])[CH3:31])[N:15]=[CH:16][C:17]=2[CH2:18][N:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=2)[C:4]1=[O:3])[CH3:10]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 10426Diphosgene

HCID 86629447HCID 86629447, compound

Product 1

HCID 86629449HCID 86629449, compoundYield 80%

Procedure

Diphosgene (2.4 mL, 20 mmol), N4-ethyl-5-((4-fluoro-3-nitrophenylamino)methyl)-N2-methoxy-N2-methylpyridine-2,4-diamine (5.6 g, 16 mmol) and Et3N (4.3 g, 40 mmol) were combined by the procedure of Example A4 to provide 1-ethyl-3-(4-fluoro-3-nitrophenyl)-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (4.8 g, 80% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.14 (m, 1 H), 7.96 (s, 1 H), 7.79 (m, 1 H), 7.61 (m, 1 H), 6.57 (s, 1 H), 4.78 (s, 2 H), 3.88 (d, J=7.2 Hz, 2 H), 3.71 (s, 3 H), 3.15 (s, 3 H), 1.20 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 376.2 [M+H]+.

Sources & evidence

ORD record: ord-1004443543594d92b0bd47a12f60ed44
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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